Abstract Although previous studies have shown that acyclic β, γ-unsaturated oximes and oxime ethers do not undergo the aza-di-π-methane (ADPM) rearrangement, the 2-methyl-4, 4-diphenyl-2-vinylbut-3-enal oxime 5a, its methyl ether 5b and the 2, 2, 4, 4-tetraphenylbut-3- enal oxime 14 give the corresponding cyclopropyl derivatives 8a, 8b and 15 by the ADPM path, in a reaction that is controlled by the stability of the intermediate 1, 3-biradical.
[Armesto, Diego; Ortiz, Maria J.; Ramos, Ana; Horspool, William M.; Mayoral, Elena P. Journal of Organic Chemistry, 1994 , vol. 59, # 26 p. 8115 - 8124]
